- Solvent-Dependent Cyclization of 2-Alkynylanilines and ClCF2COONa for the Divergent Assembly of N-(Quinolin-2-yl)amides and Quinolin-2(1 H)-ones
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Herein, we present an expedient Cu-catalyzed [5 + 1] cyclization of 2-alkynylanilines and ClCF2COONa to divergent construction of N-(quinolin-2-yl)amides and quinolin-2(1H)-ones by regulating the reaction solvents. Notably, nitrile acts as a solvent and performs the Ritter reactions. ClCF2COONa is used as a C1 synthon in this transformation, which also represents the first example for utilization of ClCF2COONa as an efficient desiliconization reagent. The current protocol involves in situ generation of isocyanide, copper-activated alkyne, Ritter reaction and protonation.
- Wang, Ya,Zhou, Yao,Ma, Xingxing,Song, Qiuling
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supporting information
p. 5599 - 5604
(2021/08/01)
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- Copper-Catalyzed Trifluoromethylation/Cyclization of Alkynes for Synthesis of Dioxodibenzothiazepines
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A facile and efficient approach for the synthesis of the CF3-containing dioxodibenzothiazepines has been developed via copper-catalyzed trifluoromethylation/cyclization of alkynes utilizing a radical relay strategy. This method has demonstrated low cataly
- Zhang, Zi-Qi,Xu, Yi-Hao,Dai, Jing-Cheng,Li, Yan,Sheng, Jie,Wang, Xi-Sheng
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supporting information
p. 2194 - 2198
(2021/04/05)
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- Sequential Sonogashira/intramolecular aminopalladation/cross-coupling ofortho-ethynyl-anilines catalyzed by a single palladium source: rapid access to 2,3-diarylindoles
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We have developed a practical and efficient one-pot protocol for the synthesis of 2,3-diarylindolesviaPd-catalyzed bis-arylative cyclization of variouso-ethynylanilines with aryl iodides. Mechanism studies showed that a Pd-catalyzed Sonogashira reaction took place firstly, giving an internal alkyne intermediate, which subsequently underwent intramolecular aminopalladation/cross-coupling to give access to 2,3-diarylindoles. The present methodology exhibits a broad substrate scope, producing various 2,3-diaryl indoles bearing two different aryl groups.
- Wang, Jiwei,Wang, Gendi,Cheng, Xiang,Liu, Ye,Zhang, Jun
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supporting information
p. 1329 - 1333
(2021/02/26)
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- New indolo[1,2-c]quinazolines for single-crystal field-effect transistor: A united experimental and theoretical studies
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Here, we account the synthesis and characterization of a series of symmetrical fused heterocyclic aromatic hydrocarbons (HAHs) with an indolo[1,2-c]quinazoline (IQ) as the core moiety. All the new HAHs IQ series were systematically investigated by using various spectroscopic methods. Furthermore, their photo-physical properties were supported by density functional theory (DFT) and time-dependent density functional theory (TDDFT) studies to support the experimental findings. The tetramethyl-substituted indolo[1,2-c]quinazoline (TMIQ) compound is shown to exhibit the shifted type of π–π stacking interactions, which render this series as a new semiconducting material. Single-crystal-based field-effect transistor devices of TMIQ exhibited efficient charge transport behavior, giving a p-channel field-effect mobility of 0.25 cm2?V?1?s?1 with an on/off ratio of 5 × 105.
- Puli, Venkat Swamy,Kilaru, Suresh,Bhongiri, Yadagiri,Marri, Sreenath Reddy,Tripathi, Anuj,Chetti, Prabhakar,Chatterjee, Anindita,Vukoti, Kiran Kumar,Pola, Someshwar
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- Photoinduced Radical Cascade Cyclization: A Metal-Free Approach to Access Difluoroalkylated Dioxodibenzothiazepines
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A simple and mild photoredox catalytic approach to access difluoroalkylated dioxodibenzothiazepines in high regioselectivity via radical cascade cyclization has been described herein. In contrast to previous methods, this strategy does not involve the use
- Deng, Yinglan,Jian, Jing-Xin,Lu, Maojian,Tong, Qing-Xiao,Xiao, Qian,Zhong, Jian-Ji
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supporting information
p. 9303 - 9308
(2021/12/06)
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- DISUBSTITUTED ALKYNE DERIVATIVES
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The present invention relates to disubstituted alkyne derivatives. These compounds are useful for the prevention and/or treatment of several medical conditions including hyperproliferative disorders and diseases.
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Page/Page column 139-140
(2020/07/14)
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- Synthesis of 1H-Pyrrolo[1,2-a]indoles via Lewis Acid-Catalyzed Annulation of Propargylic Alcohols with 2-Ethynylanilines
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A novel highly efficient, environmentally benign Lewis acid-catalyzed, and protection-free protocol for the construction of valuable polycyclic products bearing a 1H-pyrrolo[1,2-a]indole scaffold is described, starting from readily available propargylic alcohols and 2-ethynylanilines. The one-pot transformation entails the cleavage of one C?O bond, and the construction of two C?N bonds and one C?C double bond. This unique operationally simple method is performed under mild conditions and in air, producing water as the only byproduct; it is scalable and demonstrates good functional group compatibility and broad scope.
- Du, Li-Juan,Han, Ya-Ping,Liang, Yong-Min,Zhang, Hong-Yu,Zhang, Yuecheng,Zhao, Jiquan
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supporting information
(2020/03/04)
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- Copper-Catalyzed Tandem Cross-Coupling/[2 + 2] Cycloaddition of 1,6-Allenynes with Diazo Compounds to 3-Azabicyclo[5.2.0] Ring Systems
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An unprecedented copper-catalyzed tandem cross-coupling/[2 + 2] cycloaddition of 1,6-allenynes with diazo compounds was reported, chemo- and regioselectively providing 3-azabicyclo[5.2.0] frameworks in moderate to excellent yields under mild reaction conditions. Moreover, the products readily convert to highly functionalized quinolines via oxidative radical rearrangement.
- He, Min,Chen, Nuan,Zhou, Ting,Li, Qing,Li, Hongguang,Lang, Ming,Wang, Jian,Peng, Shiyong
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supporting information
p. 9559 - 9563
(2019/11/21)
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- COMPOUNDS, COMPOSITIONS, AND METHODS FOR SELECTIVELY INHIBITING β-GLUCURONIDASES AND ALLEVIATING SIDE EFFECTS ASSOCIATED WITH DRUG TREATMENT INDUCED DIARRHEA
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The present disclosure describes compounds and compositions that inhibit β-glucuronidase activity, and methods for attenuating the side effects of one or more drugs and improving the efficacy of drugs by administration of selective β-glucuronidase inhibitors.
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Page/Page column 112; 113
(2019/04/09)
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- Optimizing ligand structure for low-loading and fast catalysis for alkynyl-alcohol and-amine cyclization
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A series of [Ru(Cp/Cp?)(PR2NR′2)(MeCN)]PF6 complexes were prepared, in which the steric and electronic properties of the primary coordination sphere were varied (R = Ph, t-Bu, Bn; and Cp vs. Cp?). These complexes were catalytically active in the cyclization of alkyne substrates with an intramolecular nucleophile (amine or alcohol) to produce 5-and 6-membered heterocycles. The effect of the 1° coordination sphere structure on catalyst performance was evaluated. Steric bulk around the metal centre was a key feature to achieve rapid catalysis at low temperatures. The catalyst [Ru(Cp)(Pt-Bu2NPh2)(MeCN)]PF6 gave a turnover number that was >1 order of magnitude more active than previous catalysts in the cyclization of the benchmark substrate 2-ethynylaniline. This catalyst is tolerant of a diversity of functional groups and is competent at the formation of various substituted indoles.
- Stubbs, James M.,Bridge, Benjamin J.,Blacquiere, Johanna M.
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p. 7928 - 7937
(2019/06/13)
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- Gold-Catalyzed Intermolecular [4+2] Annulation of 2-Ethynylanilines with Ynamides: An Access to Substituted 2-Aminoquinolines
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A gold-catalyzed intermolecular [4+2] annulation of easily accessible 2-ethynylanilines with ynamides offers a highly region-selective, modular, efficient, and atom-economical strategy for the synthesis of substituted 2-aminoquinolines in up to 93% yield. (Figure presented.).
- Zhao, Ximei,Song, Xinlong,Jin, Hongming,Zeng, Zhongyi,Wang, Qian,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
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supporting information
p. 2720 - 2726
(2018/07/29)
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- Cascade Synthesis of Benzothieno[3,2- b]indoles under Oxidative Conditions Mediated by CuBr and tert-Butyl Hydroperoxide
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A series of biologically relevant compounds of benzothieno[3,2-b]indole derivatives were conveniently synthesized from reactions of N-protected 2-((2-bromophenyl)ethynyl)anilines and potassium ethylxanthate, mediated by cuprous bromide/tert-butyl hydroper
- Zhao, Xiaoyuan,Li, Qiao,Xu, Jun,Wang, Donghua,Zhang-Negrerie, Daisy,Du, Yunfei
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supporting information
p. 5933 - 5937
(2018/09/29)
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- Access to Benzo[a]carbazoles and Indeno[1,2-c]quinolines by a Gold(I)-Catalyzed Tunable Domino Cyclization of Difunctional 1,2-Diphenylethynes
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The cyclization order of the difunctional 1,2-diphenylethynes was precisely tuned under the catalysis of gold by changing the nitrogen substitution of the substrates, leading to the facile preparation of benzo[a]carbazole and indeno[1,2-c]quinoline derivatives. The mechanisms of these domino cyclizations were probed by control experiments, and an insight into the selectivity of the cyclization was gained by density functional theory (DFT) calculations. This research represents a unified and common method to access benzo[a]carbazoles and indeno[1,2-c]quinolines.
- Peng, Xiaoshi,Zhu, Lifeng,Hou, Yuqian,Pang, Yadong,Li, Yangming,Fu, Jiayue,Yang, Lu,Lin, Bin,Liu, Yongxiang,Cheng, Maosheng
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supporting information
p. 3402 - 3405
(2017/07/15)
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- CuI-Catalyzed intramolecular aminocyanation of terminal alkynes in N-(2-ethynylphenyl)-N-sulfonylcyanamides via Cu-vinylidene intermediates
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CuI-Catalyzed intramolecular aminocyanation of terminal alkynes in N-(2-ethynylphenyl)-N-sulfonylcyanamides was initiated by the formation of Cu-acetylide to trigger N-CN bond cleavage of the N-sulfonylcyanamide moiety followed by CN migration to form a β-cyano Cu-vinylidene intermediate. Subsequently, the indole ring closure furnished the corresponding 1-sulfonyl-3-cyanoindoles.
- Liao, Zhen-Yuan,Liao, Pen-Yuan,Chien, Tun-Cheng
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supporting information
p. 14404 - 14407
(2016/12/23)
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- Revisiting the Gold-Catalyzed Dimerization of 2-Ethynylanilines: A Room-Temperature and Silver-Free Protocol for the Synthesis of Multifunctional Quinolines
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A room temperature and silver-free protocol for the formation of quinolines from 2-ethynylanilines through a dimerization event was achieved using a dinuclear gold catalyst, Au2(BIPHEP)(NTf2)2. The reaction is inherently modular, allowing for the incorporation of peripheral substituents at any site of the quinoline product. The reaction is readily applied to other heterocyles also as exemplified by the preparation of naphthyridines. Competition reactions to determine the reactivity of dissimilar alkynes demonstrated that the product ratio of dimerization vs intermolecular addition is rather dependent on the electronic nature of aryl substituent on the alkynes. However, control experiments with substrates possessing internal alkynes resulted in cycloisomerization instead of expected dimerization, which is indicative of possible steric influence of the alkyne terminus in the reaction outcome.
- Praveen, Chandrasekar,Perumal
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p. 855 - 864
(2016/03/15)
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- Cs2CO3 as a source of carbonyl and ethereal oxygen in a Cu-catalysed cascade synthesis of benzofuran [3,2-: C] quinolin-6[5- H] ones
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The simultaneous construction of C-C, C-O, and C-N bonds utilizing Cs2CO3 as a source of both carbonyl (CO) and ethereal oxygen and a cascade synthesis of benzofuro[3,2-c]quinolin-6(5H)-one have been achieved using a combination of C
- Ali, Wajid,Modi, Anju,Behera, Ahalya,Mohanta, Prakash Ranjan,Patel, Bhisma K.
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supporting information
p. 5940 - 5944
(2016/07/06)
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- One-Pot Access to Benzo[a]carbazoles via Palladium(II)-Catalyzed Hetero- and Carboannulations
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A Pd(II)-catalyzed direct synthesis of benzo[a]carbazoles has been achieved through aminopalladation of alkynes, followed by intramolecular nucleophilic addition of the generated carbon-palladium bond to a tethered cyano/aldehyde group. Compared to literature procedures, this synthetic approach is operationally simple, uses simple substrates, and offers a fast intramolecular assembly resulting in the direct synthesis of benzo[a]carbazoles in which a wide variation of substituents at different sites is well-tolerated, leaving enough opportunity for diversification.
- Jash, Moumita,Das, Bimolendu,Chowdhury, Chinmay
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supporting information
p. 10987 - 10999
(2016/11/28)
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- Copper-catalyzed annulation of α-substituted diazoacetates with 2-ethynylanilines: The direct synthesis of C2-functionalized indoles
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Copper-catalyzed direct annulation of α-substituted diazoacetates with 2-ethynylanilines leading to C2-functionalized indoles was achieved under mild reaction conditions. The C2-(carboxylate methyl) substituted indoles were obtained in moderate to high yi
- Liu, Gang,Xu, Guangyang,Li, Jian,Ding, Dong,Sun, Jiangtao
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supporting information
p. 1387 - 1390
(2014/03/21)
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- Flexible and practical synthesis of 3-oxyindoles through gold-catalyzed intermolecular oxidation of o-ethynylanilines
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A novel gold-catalyzed intermolecular oxidation of o-ethynylanilines has been developed. A range of functionalized 3-oxyindoles are readily accessed by utilizing this strategy. Importantly, this gold-catalyzed oxidative process outcompetes the typical ind
- Shu, Chao,Li, Long,Xiao, Xin-Yu,Yu, Yong-Fei,Ping, Yi-Fan,Zhou, Jin-Mei,Ye, Long-Wu
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supporting information
p. 8689 - 8692
(2014/07/22)
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- 5 -CYANO-4, 6 -DIAMINOPYRIMIDINE OR 6 -AMINOPURINE DERIVATIVES AS PI3K- DELTA INHIBITORS
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Substituted bicyclic heteroaryls and compositions containing them, for the treatment of general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, including but not restricted to autoimmune diseases such as systemic lupus erythematosis (SLE), myestenia gravis, rheumatoid arthritis, acute disseminated encephalomyelitis, idiopathic thrombocytopenic purpura, multiples sclerosis, Sjoegren's syndrome and autoimmune hemolytic anemia, allergic conditions including all forms of hypersensitivity, The present invention aLso enables methods for treating cancers that are mediated, dependent on or associated with pi 105 activity, including but not restricted to leukemias, such as Acute Myeloid leukaemia (AML) Myelo- dysplastic syndrome (MDS) myelo-proliferative diseases (MPD) Chronic Myeloid Leukemia (CML) T-cell Acute Lymphoblastic leukaemia ( T-ALL) B-cell Acute Lymphoblastic leukaemia (B-ALL) Non Hodgkins Lymphoma (NHL) B-cell lymphoma and solid tumors, such as breast cancer.
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Page/Page column 49
(2012/05/20)
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- Direct synthesis of polysubstituted quinoline derivatives by InBr 3-promoted dimerization of 2-ethynylaniline derivatives
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InBr3 promotes the dimerization of 2-ethynylaniline derivatives containing an unsubstituted terminal carbon leading to the production of polysubstituted quinoline derivatives in good yield.
- Sakai, Norio,Annaka, Kimiyoshi,Konakahara, Takeo
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p. 3653 - 3655
(2007/10/03)
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